The invention provides a compound having the general formula (I): 
and stereoisomers thereof, wherein X, Y and Z, which may be the same or different, are hydrogen or halogen atoms, or optionally substituted alkyl, optionally substituted alkenyl, optionally substituted aryl, optionally substituted alkynyl, haloalkyl, alkoxy, haloalkoxy, optionally substituted aryloxy, optionally substituted arylalkoxy, optionally substituted acyloxy, optionally substituted amino, optionally substituted arylazo, acylamino, nitro, nitrile, xe2x80x94CO2R3, xe2x80x94CONR4R5, xe2x80x94COR6, xe2x80x94CR7xe2x95x90NR8, or xe2x80x94Nxe2x95x90CR9R10 groups or the groups X and Y, when they are in adjacent positions on the phenyl ring, may join to form a fused ring, either aromatic or aliphatic, optionally containing one or more heteroatoms; and R1, R2, R3, R4, R5, R6, R7, R8, R9, and R10, which may be the same or different, are hydrogen atoms or alkyl, cycloalkyl, alkenyl, alkynyl, optionally substituted aryl, optionally substituted aralkyl, or cycloalaylalkyl groups; and metal complexes thereof.
The compounds of the invention contain at least one carbon-carbon double bond, and are sometimes obtained in the form of mixtures of geometric isomers. However, these mixtures can be separated into individual isomers, and this invention embraces such isomers.
Alkyl groups can be in the form of straight or branched chains, and preferably contain 1 to 6 carbon atoms; examples are methyl, ethyl, propyl, (n- or iso-propyl) and butyl (n-, sec-, iso- or t-butyl). The methyl group is the preferred alkyl group for both R1 and R2.
In a further aspect the invention provides compounds having the general formula (I): 
and stereoisomers thereof, wherein X, Y and Z, which may be the same or different, are hydrogen or halogen atoms, or optionally substituted alkyl, optionally substituted alkenyl, optionally substituted aryl, optionally substituted alkynyl, haloalkyl, alkoxy, haloalkoxy, optionally substituted aryloxy, optionally substituted arylalkoxy, amino, acylamino, nitro, nitrile, xe2x80x94CO2R3, xe2x80x94CONR4R5, or xe2x80x94COR6 groups; and R1, R2, R3, R4, R5 and R6, which may be the same or different, are hydrogen atoms or alkyl, cycloalkyl, alkenyl, alkynyl, optionally substituted aryl, optionally substituted aralkyl, or cycloalkylalkyl groups; and metal complexes thereof.
In another aspect the invention provides compounds having the general formula (I): 
and stereoisomers thereof, wherein X, Y and Z, which may be the same or different, are hydrogen or halogen atoms, or optionally substituted alkyl, optionally substituted alkenyl, optionally substituted aryl, optionally substituted alkynyl, haloalkyl, alkoxy, optionally substituted aryloxy, optionally substituted arylalkoxy, optionally substituted amino, xe2x80x94CO2R3, xe2x80x94COR6 groups, or the groups X and Y, when they are in adjacent positions on the phenyl ring, may join to form a fused aromatic ring; and R1, R2, R3 and R6, which may be the same or different, are alkyl, optionally substituted phenyl, or optionally substituted aralkyl groups.
In a still further aspect the invention provides compounds having the general formula (I): 
and stereoisomners thereof, wherein X, Y and Z, which may be the same or different, are hydrogen, fluorine, chlorine or bromine atoms, or C1-4 alkyl, C2-5 alkenyl, C2-5 alkynyl, phenyl, C1-4 haloalkyl, C1-4 alkoxy, phenoxy, benzyloxy or mono- or dialkylamino groups, or the groups X and Y, when they are in adjacent positions on the phenyl ring, join to form a fused aromatic ring, the aliphatic moieties of any of the foregoing being optionally substituted with one or more C1-4 alkoxy groups, fluorine, chlorine or bromine atoms, phenyl rings which themselves are optionally substituted, heterocyclic rings which are either aromatic or non-aromatic and are themselves optionally substituted, nitro, amino, nitrile, hydroxyl or carboxyl groups; and wherein the phenyl moieties of any of the foregoing are optionally substituted with one or more fluorine, chlorine or bromine atoms, phenyl rings, C1-4 alkyl, C1-4 alkoxy, nitro, amino, nitrile, hydroxyl or carboxyl groups; and R1 and R2, which may be the same or different, are C1-4 alkyl, phenyl or benzyl groups, each optionally substituted with halogen atoms.
In yet another aspect the invention provides compounds having the general formula (XI): 
wherein R is an optionally substituted phenyl or an optionally substituted benzyl group, and Y is a hydrogen of a halogen (fluorine, chlorine or bromine) atom or a methyl, methoxyl, nitro, nitrile, carboxyl or methoxycarbonyl group.
In another aspect the invention provides compounds having the general formula (XII): 
and stereoisomers thereof, wherein X is an alkyl, alkenyl, alkynyl, aryloxy or arylalkoxy group, each of which is optionally substituted.
In a further aspect the invention provides compounds having the general formula (XIII): 
and stereoisomers thereof, wherein X is an optionally substituted alkyl, optionally substituted alkenyl, or optionally substituted alkynyl group.
In particular the invention, in a still further aspect, provides compounds wherein the optional substituents in the foregoing paragraph are phenyl, itself optionally substituted with one or more of the following: fluorine, chlorine, bromine, C1-4 alkyl (especially methyl), C1-4 alkoxy (especially methoxy), or nitro.
In a still further aspect the invention provides compounds having the general formula (XIV): 
and stereoisomers thereof, wherein X is an optionally substituted aryloxy group or an optionally substituted arylalkoxy group.
In the foregoing paragraph X can be phenoxy or benzyloxy, either of which can be optionally substituted with one or more halogens (fluorine, chlorine or bromine) or a methyl, methoxyl, ethyl, ethoxyl, nitro, nitrile, carboxyl or methoxycarbonyl group.
In a yet further aspect the invention provides compound having the general formula (XV): 
and stereoisomers thereof, wherein X, Y and Z, which may be the same or different, are fluorine, chlorine, bromine, or hydrogen atoms, or methyl, methoxyl or nitro groups.
The invention provides the compounds: 
(compound number 9 of Table I below). 
(Compound number 13 of Table I below). 
(Compound number 19 of Table I below). 
(Compound number 1 of Table II below). 
(Compound number 1 of Table IV below).
Table III below embraces compounds of the general formula: 
wherein the group R includes all the groups R listed in Table II for each of the following substitution patterns on the phenyl ring shown above. The acrylate group may have either the E- or the Z-geometry in each case.
Specific examples of compounds of the type shown in Table III are as follows:
Table V embraces compounds of the general formula:
wherein the group R includes all the group R listed in Table IV for each of the following substitution patterns on the phenyl ring shown above. The acrylate group may have either the E- or the Z-geometry in each case.
The compounds of the invention having the general formula (I) can be prepared from substituted benzenes of general formula (IV) by the steps shown in Scheme I. Throughout Scheme I the terms R1, R2, X, Y and Z are as defined above, L is a halogen (iodine, bromine or chlorine) atom or a hydrogen atom, and M is a metal atom (such as a lithium atom) or a metal atom plus as associated halogen atom (such as MgI, MgBr or MgCl).
Thus compounds of general formula (I) in which R1 and R2 are not hydrogen atoms can be prepared by treatment of ketoesters of general formula (II: R1 is not a hydrogen atom) with phosphoranes of general formula (V: R2 is not a hydrogen atom) in a convenient solvent such as diethyl ether (see, for example, W I Steglich, G Schramm, T Anke and F Oberwinkler, EP 0044448, 4.7.80).
Ketoesters of general formula (II: R1 is not a hydrogen atom) can be prepared by treatment of metallated species (III) with an oxalate (VI, R1 is not a hydrogen atom) in a suitable solvent such as diethyl ether or tetrahydrofuran. The preferred method often involves slow addition of a solution of the metallated species (III) to a stirred solution of an excess of the oxalate (VI) (see, for example, L M Weinstock, R B Currie and A V Lovell, Synthetic Communications, 1981, 11, 943, and references therein).
The metallated species (III) in which M=MgI, MgBr or MgCl (Grignard reagents) can be prepared by standard methods from the corresponding aromatic halides (IV) in which L=I, Br or Cl respectively. With certain substituents X, Y and Z, the metallated species (III) in which M=Li can be prepared by direct lithiation of compounds (IV) in which L=H using a strong lithium base such as n-butyl-lithium or lithium di-isopropylamide (see, for example, H W Gschwend and H R Rodriguez, Organic Reactions, 1979, 26, 1).
Compounds of general formula (IV) can be prepared by standard methods described in the chemical literature. 
Alternative methods for the preparation of ketoesters of general formula (II: R1 is not a hydrogen atom) are described in the chemical literature (see, for example, D C Atkinson, K E Godfrey, B Meek, J F Saville and M R Stillings, J. Med. Chem., 1983, 26, 1353; D Horne, J Gaudino and W J Thompson, Tetrahedron Lett., 1984, 25, 3529; and G P Axiotis, Tetrahedron Lett., 1981, 22, 1509).
Alternative approaches to the compounds of the invention of general formula (I) are outlined in Scheme II. Throughout Scheme II the terms R1, R2, X, Y and Z are as defined above. 
Compounds of general formula (I) in which R1 is not a hydrogen atom can be prepared by treatment of phenylacetates of general formula (VII: R1 is not a hydrogen atom) with a base and a formic ester such as methyl formate or HCO2R1 wherein R1 is as defined above but is not a hydrogen atom, in a suitable solvent. If the reaction is quenched with a species of general formula R2Q, wherein R2 is as defined above but it is not a hydrogen atom and Q is a leaving group such as a halogen atom, compounds of general formula (I) in which R2 is not a hydrogen atom may be obtained. If, on the other hand, the reaction is quenched with water, compounds of general formula (I) in which R2xe2x95x90H are obtained.
Compounds of general formula (I) in which R2xe2x95x90H can be converted into compounds (I) in which R2 is not a hydrogen atom by successive treatment with a base (such as potassium carbonate or sodium hydride) and a species of general formula R2Q, wherein R2 and Q are as defined above, in a suitable solvent.
Furthermore, compounds of general formula (I) in which neither R1 nor R2 are hydrogen atoms can be made from acetals of general formula (VIII) in which neither R1 nor R2 are hydrogen atoms under either basic or acidic conditions, in suitable solvents and at suitable temperatures. An example of a suitable base is lithium di-isopropylamide, and potassium hydrogen sulphate is an example of a suitable acidic reagent (see T Yamada, H Hagiwara and H Uda, Journal of the Chem. Soc., Chem. Commun., 1980, 838, and references therein).
Acetals of general formula (VIII) in which neither R1 nor R2 are hydrogen atoms may be prepared from phenylacetic esters of general formula (VII: R1 is not a hydrogen atom) by treatment of alkyl silyl ketene acetal derivatives of the species (VII) with trialkylorthoformates in the presence of a Lewis acid in a suitable solvent and at a suitable temperature (sees for example, K Saigo, M Osaki and T Mukaiyama, Chem. Letts., 1976, 769).
Alternative approaches to the compounds of the invention of general formula (I) are outlined in Scheme III. Throughout Scheme III the terms R1, R2, X, Y and Z are as defined above. 
Thus, compounds of general formula (I) in which R1 is not a hydrogen atom and R2xe2x95x90H can be made by partial reduction of malonate derivatives (IX: R1 is not a hydrogen atom) using a reducing agent such as lithium aluminium hydride in a suitable solvent such as diethyl ether (see, for example, M Barczai-Beke, G Dornyei, G Toth, J Tamas and Cs Szantay, Tetrahedron, 1976, 32, 1153, and references therein).
In addition, compounds of general formula (I) can be made from acrylic acid derivatives of general formula (X) by successive treatment with bromine, a reagent of general formula R2OM, wherein R2 and M are as defined above, and sodium hydrogen sulphate or a related chemical (see, for example, G Shaw and R N Warrener, Journal of the Chemical Society, 1958, 153, and references therein).
Compounds of general formulae. (VII), (IX) and (X) can be prepared by standard methods described in the chemical literature.
All the foregoing processes, either in full, or in any part (step) or parts (steps) thereof, in any combination thereof, are deemed to constitute processes according to the invention.
The compounds and metal complexes of the invention are active fungicides, particularly against the diseases
Pyricularia oryzae on rice Puccinia recondita, Puccinia striiformis and other rusts on wheat, Puccinia hordei, Puccinia striiformis and other rusts on barley, and rusts on other hosts eg. coffee, pears, apples, peanuts, vegetables and ornamental plants.
Erysiphe graminis (powdery mildew) on barley and wheat and other powdery mildews on various hosts such as Sphaerotheca macularis on hops Sphaerotheca fuliginea on cucurbits (eg. cucumber), Podosphaera leucotricha on apples and Uncinula necator on vines.
Helminthosporium spp., Rhynchosporium spp., Septoria spp., Pseudocercosporella herpotrichoides and Gauomannomyces graminis on cereals. Cercospora arachidicola and Cercosporidium personata on peanuts and other Cercospora species on other hosts for example sugar beet, bananas, soya beans and rice. Botrytis cinerea (grey mould) on tomatoes, strawberries, vegetables, vines and other hosts.
Alternaria species on vegetables (eg. cucumber), oil seed rape, apples, tomatoes and other hosts.
Venturia inaequalis (scab) on apples Plasmopara viticola on vines Other downy mildews such as Bremia lactucae on lettuce, Peronospora spp. on soybeans, tobacco, onions and other hosts and Pseudoperonospora humuli on hops and Pseudoperonospora cubensis on cucurbits Phytophthora infestans on potatoes and tomatoes and other Phytophthora spp. on vegetables, strawberries, avocado, pepper, ornamentals, tobacco, cocoa and other hosts.
Thanatephorus cucumeris on rice and other Rhizoctonia species on various hosts such as wheat and barley, vegetables, cotton and turf.
Some of the compounds have also shown a broad range of activities against fungi in vitro. They have activity against various post-harvest diseases of fruit (eg. Penicillium digitatum and italicum and Trichoderma viride on oranges and Gloesporium musarum on bananas).
Further some of the compounds are active as seed dressings against Fusarium spp., Septoria spp., Tilletia spp. (bunt, a seed borne disease of wheat), Ustilago spp., Helminthosporium spp. on cereals, Rhizoctonia solani on cotton and Pyricularia oryzae on rice.
The compounds can move acropetally in the plant tissue. Moreover, the compounds can be volatile enough to be active in the vapour phase against fungi on the plant.
The compounds may also be useful as industrial (as opposed to agricultural) fungicides, eg. in the prevention of fungal attack on wood, hides, leather and especially paint films.
Some of the compounds exhibit herbicidal activity and at the appropriately higher rate of application may be used to combat weeds.
Similarly, some compounds exhibit plant growth regulating activity and may be deployed for this purpose, again at appropriate rates of application.
This invention, therefore, includes the foregoing uses of the compounds (and compositions containing them) in addition to their principal use as fungicides.
The compounds may be used as such for fungicidal purposes but are more conveniently formulated into compositions for such usage. The invention thus provides a fungicidal composition comprising a compound of general formula (I) as hereinbefore defined, or a metal complex thereof; and, optionally, a carrier or diluent.
The invention also provides a method of combating fungi, which comprises applying to a plant, to seed of a plant, or to the locus of the plant or seed, a compound or metal complex thereof, as hereinbefore defined.
The compounds and metal complexes of the invention can be applied in a number of ways. For example they can be applied, formulated or unformulated, directly to the foliage of a plant, or they can be applied also to bushes and trees, to seeds or to other medium in which plants, bushes or trees are growing or are to be planted, or they can be sprayed on, dusted on or applied as a cream or paste formulation, or they can be applied as a vapour; or as slow release granules. Application can be to any part of the plant, bush or tree, for example to the foliage, stems, branches or roots, or to soil surrounding the roots, or to the seed before it is planted; or to the soil generally, to paddy water or to hyroponic culture systems. The invention compounds may also be injected into plants or trees and they may also be sprayed onto vegetation using electrodynamic spraying techniques, or other low volume methods.
The term xe2x80x9cplantxe2x80x9d as used herein includes seedlings, bushes and trees. Furthermore, the fungicidal method of the invention includes preventative, protectant, prophylactic and eradicant treatment.
The compounds are preferably used for agricultural and horticultural purposes in the form of a composition. The type of composition used in any instance will depend upon the particular purpose envisaged.
The compositions may be in the form of dusting powders or granules comprising the active ingredient and a solid diluent or carrier, for example fillers such as kaolin, bentonite, kieselguhr, dolomite, calcium carbonate, talc, powdered magnesia, Fuller""s earth, gypsum, Rewitt""s earth, diatomaceous earth and China clay. Such granules can be preformed granules suitable for application to the soil without further treatment. These granules can be made either by impregnating pellets of filler with the active ingredient or by pelleting a mixture of the active ingredient and powdered filler. Compositions for dressing seed, for example, may comprise an agent (for example a mineral oil) for assisting the adhesion of the composition to the seed; alternatively the active ingredient can be formulated for seed dressing purposes using an organic solvent (for example N-methylpyrrolidone or dimethylformamide).
The compositions may also be in the form of dispersible powders, granules or grains comprising a wetting agent to facilitate the dispersion in liquids of the powder or grains which may contain also fillers and suspending agents.
The aqueous dispersions or emulsions may be prepared by dissolving the active ingredient(s) in an organic solvent optionally containing wetting, dispersing or emulsifying agent(s) and then adding the mixture to water which may also contain wetting, dispersing or emulsifying agent(s). Suitable organic solvents are ethylene dichloride, isopropyl alcohol, propylene glycol, diacetone alcohol, toluene, kerosene, methylnaphthalene, the xylenes, trichloroethylene, furfuryl alcohol, tetrahydrofurfuryl alcohol, and glycol ethers (eg. 2-ethoxyethanol and 2-butoxyethanol).
The compositions to be used as sprays may also be in the form of aerosols wherein the formulation is held in a container under pressure in the presence of a propellant, eg. fluorotrichloromethane or dichlorodifluoromethane.
The compounds can be mixed in the dry state with a pyrotechnic mixture to form a composition suitable for generating in enclosed spaces a smoke containing the compounds.
Alternatively, the compounds may be used in a micro-encapsulated form. They may also be formulated in biodegradable polymeric formulations to obtain a slow, controlled release of the active substance.
By including suitable additives, for example additives for improving the distribution, adhesive power and resistance to rain on treated surfaces, the different compositions can be better adapted for various utilities.
The compounds can be used as mixtures with fertilisers (eg. nitrogen-, potassium- or phosphorus-containing fertilisers). Compositions comprising-only granules of fertiliser incorporating, for example coated with, the compound are preferred. Such granules suitably contain up to 25% by weight of the compound. The invention therefore also provides a fertiliser composition comprising the compound of general formula (I) or metal complex thereof.
The compositions may also be in the form of liquid preparations for use as dips or sprays which are generally aqueous dispersions or emulsions containing the active ingredient in the presence of one or more surfactants eg. wetting agent(s), dispersing agent(s), emulsifying agent(s) or suspending agent(s); or which are spray formulations of the kind suitable for use in electrodynamic spraying techniques. The foregoing agents can be cationic, anionic or non-ionic agents. Suitable cationic agents are quaternary ammonium compounds, for example cetyltrimethylammonium bromide.
Suitable anionic agents are soaps, salts of aliphatic monoesters of sulphuric acid (for example sodium lauryl sulphate), and salts of sulphonated aromatic compounds (for example sodium dodecylbenzenesulphonate, sodium, calcium or ammonium lignosulphonate, butylnaphthalene sulphonate, and a mixture of sodium diisopropyl- and triisopropylnaphthalene sulphonates).
Suitable non-ionic agents are the condensation products of ethylene oxide with fatty alcohols such as oleyl or cetyl alcohol, or with alkyl phenols such as octyl- or nonyl-phenol and octylcresol. Other non-ionic agents are the partial esters derived from long chain fatty acids and hexitol anhydrides, the condensation products of the said partial esters with ethylene oxide, and the lecithins. Suitable suspending agents are hydrophilic colloids (for example polyvinylpyrrolidone and sodium carboxymethylcellulose), and the vegetable gums (for example gum acacia and gum tragacanth).
The compositions for use as aqueous dispersions or emulsions are generally supplied in the form of a concentrate containing a high proportion of the active ingredient(s), and the concentrate is to be diluted with water before use. These concentrates often should be able to withstand storage for prolonged periods and after such storage be capable of dilution with water in order to form aqueous preparations which remain homogeneous for a sufficient time to enable them to be applied by conventional and electrodynamic spray equipment. The concentrates may conveniently contain up to 95%, suitably 10-85%, for example 25-60%, by weight of the active ingredient(s). These concentrates suitably contain organic acids (eg. alkaryl or aryl sulphonic acids such as xylenesulphonic acid or dodecyl benzenesulphonic acid) since the presence of such acids can increase the solubility of the active ingredient(s) in the polar solvents often used in the concentrates. The concentrates suitably contain also a high proportion of surfactants so that sufficiently stable emulsions in water can be obtained. After dilution to form aqueous preparations, such preparations may contain varying amounts of the active ingredient(s) depending upon the intended purpose, but an aqueous preparation containing 0.0005% or 0.01% to 10% by weight of active ingredient(s) may be used.
The compositions of this invention can comprise also other compound(s) having biological activity, eg. compounds having similar or complementary fungicidal activity or compounds having plant growth regulating, herbicidal or insecticidal activity.
The other fungicidal compound can be, for example, one which is capable of combating ear diseases of cereals (eg. wheat) such as Septoria, Gibberella and Helminthosporium spp., seed and soil borne diseases and downy and powdery mildews on grapes and powdery mildew and scab on apple etc. These mixtures of fungicides can have a broader spectrum of activity than the compound of general formula (I) alone; further, the other fungicide can have a synergistic effect on the fungicidal activity of the compound of general formula (I). Examples of the other fungicidal compounds are carbendazim, benomyl, thiophanate-methyl, thiabendazole, fuberidazole, etridazole, dichlofluanid, cymoxanil, oxadixyl, ofurace, metalaxyl, furalaxyl, benalaxyl, fosetyl aluminium, fenarimol, iprodione, procymidione, vinclozolin, penconazole, myclobutanil, R0151297, S3308, pyrazophos, ethirimol, ditalimfos, tridemorph, triforine, nuarimol, triazbutyl, guazatine, propiconazole, prochloraz, flutriafol, chlortriafol ie. the chemical 1-(1,2,4-triazol-1-yl)-2-(2,4-dichlorophenyl)-hexan-2-ol, DPX H6573(1-((bis-4-fluorophenyl)methylsilyl)methyl)-1H-1,2,4-triazole, triadimefon, triadimenol, diclobutrazol, fenpropimorph, fenpropidine, triademorph, imazalil, fenfuram, carboxin, oxycarboxin, methfuroxam, dodemorph, BAS 454, blasticidin S, Kasugamycin, edifenphos, kitazin P, phthalide, probenazole, isoprothiolane, tricyclazole, pyroquilan, chlorbenzthiazone, neoasozin, polyoxin D, validamycin A, repronil, flutolanil, pencycuron, diclomezine, phenazin oxide, nickel dimethyldithiocarbamate, techlofthalam, bitertanol, bupirimate, etaconazole, streptomycin, cypofuram, biloxazol, quinomethionate, dimethirimol, fenapanil, tolclofos-methyl, pyroxyfur, polyram, maneb, mancozeb, captafol, chlorothalonil, anilazine, thiram, captan, folpet, zineb, propineb, sulphur, dinocap, binapacryl, nitrothal-isopropyl, dodine, dithianon, fentin hydroxide, fentin acetate, tecnazene, quintozene, dichloran, copper containing compounds such as copper oxychloride, copper sulphate and Bordeaux mixture, and organomercury compounds such as 1-(2-cyano-2-methoxyiminoacetyl)-3-ethyl urea.
The compounds of general formula (I) can be mixed with soil, peat or other rooting media for the protection of plants against seed-borne, soil-borne or foliar fungal diseases.
Suitable insecticides are pirimicarb, di-methoate, demeton-s-methyl, formothion, carbaryl, isoprocarb, XMC, BPMC, carbofuran, carbosulfan, diazinon, fenthion, fenitrothion, phenthoate, chlorpyrifos, isoxathion, propaphos, monocrotophas, buprofezin, ethroproxyfen and cycloprothrin.
The plant growth regulating compound can be one which controls weeds or seedhead formation, or selectively controls the growth of the less desirable plants (eg. grasses).
Examples of suitable plant growth regulating compounds, for use with the invention compounds are the gibberellins (eg. GA3, GA4 or GA7), the auxins (eg. indoleacetic acid, indolebutyric acid, naphthoxyacetic acid or naphthylacetic acid), the cytokinins (eg. kinetin, diphenylurea, benzimidazole, benzyladenine or benzylaminopurine), phenoxyacetic acids (eg. 2,4-D or MCPA), substituted benzoic acids (eg. triiodobenzoic acid), morphactins (eg. chlorfluorecol), maleic hydrazide, glyphosate, glyphosine, long chain fatty alcohols and acids, dikegulac, paclobutrazol, flurprimidol, fluoridamid, mefluidide, substituted quaternary ammonium and phosphonium compounds (eg. chlormequat, chlorphonium or mepiquatchloride), ethephon, carbetamide, methyl-3,6-dichloroanisate, daminozide, asulam, abscisic acid, isopyrimol, 1-(4-chlorophenyl)-4,6-dimethyl-2-oxo-1,2-dihydropyridine-3-carboxylic acid, hydroxybenzonitriles (eg. bromoxynil), difenzoquat, benzoylprop-ethyl 3,6-dichloropicolinic acid, paclobutrazol, fenpentezol, inabenfide, triapenthenol and tecnazene.
The following Examples illustrates the invention. Throughout these examples, the term xe2x80x9cetherxe2x80x9d refers to diethyl ether, magnesium sulphate was used to dry solutions, and reactions involving water-sensitive intermediates were performed under atmospheres of nitrogen. Unless otherwise stated, chromatography was performed using silica gel as the stationary phase. Where shown, infrared and nmr data are selective; no attempt is made to list every absorption. The following abbreviations are used throughout: